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Catalytic asymmetric total syntheses of (R)-bgugaine and (R)-irnidine
Tetrahedron ( IF 2.1 ) Pub Date : 2020-11-28 , DOI: 10.1016/j.tet.2020.131789
Christopher J. Maddocks , Paul A. Clarke

An enantioselective total synthesis of (R)-bgugaine and the first enantioselective total synthesis of (R)-irnidine are reported. The key steps are the asymmetric ‘clip-cycle’ formation of the pyrrolidine ring in 94:6 e.r., which is common to both natural products, followed by Liebeskind–Srogl coupling and Wolf-Kishner reduction. The route yields (R)-bgugaine and (R)-irnidine in 6 steps and in overall yields of 33% and 18% respectively.



中文翻译:

R)-双胍丁胺和(R)-乙啶的催化不对称全合成

的对映体选择性全合成(- [R)-bgugaine和(的第一对映选择性全合成- [R)-irnidine报告。关键步骤是在94:6 er中吡咯烷环的不对称“剪切循环”形成,这对两种天然产物都是常见的,随后是Liebeskind-Srogl偶联和Wolf-Kishner还原。该路线分6步产生(R)-古吉ine碱和(R)-亚氨酸idine,总产率分别为33%和18%。

更新日期:2020-12-17
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